Rock ’N’ Roll Fantasy Stripped Bare

Another slog through Europe, and Dean Wareham, respected, almost-famous singer and guitarist, is finally realizing that elusive rock ’n’ roll fantasy. An Andalusian beauty with a “fantastic chest” is making eyes at him through the whole show. Afterward, she takes him home. She’s a flight attendant, and rather than slip into something more comfortable, she actually dons her uniform for the night’s proceedings. His conscience goes missing as they cavort until dawn. His penance begins when she sings him her favorite song: “More Than Words,” by Extreme.

Black Postcards, Mr. Wareham’s memoir about strumming away in relative obscurity, is full of anecdotes like this one. Every setup is followed by a letdown, every hope answered with embarrassment or frustration. That’s probably because over a couple decades in the business, Mr. Wareham, with his two critically lauded zero-hit wonders, Galaxie 500 and Luna, may have earned “greatest band you’ve never heard of” status from Rolling Stone and a berth on Pitchfork’s favorites from the 80’s list—but he’s seen little in the way of profits and a fair measure of grief.

So don’t expect too many rosy pictures: If there’s a message scrawled across Black Postcards, it’s not “wish you were here.” There are no moments of lasting glamour in these pages, a lot of interpersonal pitfalls and a great view of a dysfunctional recording industry.

A lot like Mr. Wareham’s music: kind of a downer, but compelling.

THE BOOK BREEZES through Mr. Wareham’s birth in New Zealand and youth in Manhattan. He feels like an outsider at rich-kid Dalton, where he meets future Galaxie 500 drummer Damon Krukowski. His high-school crew revels in a New York scene that mattered (and apparently carded less stringently)—CBGB, the Mudd Club, Talking Heads, the Ramones. “We were … part-time punks,” Mr. Wareham admits, “private-school kids dressing up as something we were not.” He makes it to Harvard, doesn’t study very much and expands his tastes beyond punk and new wave.

A couple years after college, he hits on the dreamy, meandering guitar sound and adenoidal twang that will define Galaxie 500. The arty, mopey trio allows him his first glimpses of indie success—a small but devoted following, hyperbole from the U.K. music mags. It also reveals a downside: hours upon hours with the same few people crammed into rehearsal spaces, unreliable vans and dingy venues.

Tension with Mr. Krukowski (whose girlfriend, Naomi Yang, is the bassist) gnaws at him until he instigates the first big breakup of the book. It’s clearly a torturous decision for him—one for which he has been vilified—and he writes about it defensively. His ex-bandmates and fans assume his sudden departure is driven by greed and ego. He instead paints Mr. Krukowski as a control freak and himself more like a passive luftmensch who just couldn’t stand the cult-like dynamic of the trio.

Eventually, fans and critics forgive him, around the time Luna, his catchier follow-up band, release their second album. There are interesting characters from this period, too—another surly drummer, a second guitarist who obsesses over every note of his solos—but the most remarkable thing about the Luna story is the way it maps the sad trajectory of the record industry.

MR. WAREHAM EXPLAINS how in the late 80’s, “the lean years of hair metal and John Cougar Mellencamp,” bands like his were indie because there was no other option. Post-Nirvana, though, the majors go on a frenzy, hoping to score the next alt-rock stars. “Bands were signed left and right and stores were selling a ton of CDs.” Elektra signs Luna, ushering them into the world of recoupable advances, royalty agreements and excessive studio budgets, all tied together with the industry’s byzantine brand of loopy accounting.

One night, legendary record mogul Seymour Stein wines and dines the band. He lisps a grievance about the state of the industry: “So many little boats, the big boats can’t get out to sea. It’s terrible.” (Given today’s situation, as boats of all shape and size sail freely from pier to pier with nary a thought of bandwidth, I’ll bet Mr. Stein wouldn’t mind returning to that quaint overcrowded harbor.)

Too delicate for grungified MTV, too cerebral for VH1’s “adult alternative,” Mr. Wareham helms a little boat for Elektra. While the rest of the industry rides to its late-90’s crest on the backs of boy bands and tween-worshiped temptresses, Luna is ahead of the rest, already sliding down to the uncharted trough. Without a radio hit to their name, they’re dropped by their label, their publisher and, most insultingly, their accountant. They persevere through personnel changes (Britta Phillips joins as new bassist/home-wrecker), dwindling returns and difficult tours.

Their slow fizzle stands in contrast to the earlier blowout, but as the end draws near, you see the writing on the wall: A rock band is a breakup waiting to happen. And you wonder if Mr. Wareham’s guilty assessment of his little Spanish fling might not apply to the whole game: “You have to pay for the good times.”